Hydrochloric Acid → 2-(4-Nitrophenyl)benzofuran-7-carboxylic acid

HRID 1761926Notes

Reaction equation

HRID 1761926 reaction equation
[CH:1]([C:3]1[C:4]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8]C)=[O:7])=O.C[O-].[Na+].Cl>CN(C)C=O.CO>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([C:14]2[O:13][C:4]3[C:5]([C:6]([OH:8])=[O:7])=[CH:10][CH:11]=[CH:12][C:3]=3[CH:1]=2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 20043641Methyl 3-formyl-2-(4-nitrobenzyloxy)benzoate

Product 1

HCID 142297282-(4-Nitrophenyl)benzofuran-7-carboxylic acidYield 59.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

16.1 g of methyl 3-formyl-2-(4-nitrobenzyloxy)benzoate are dissolved in 100 ml of dimethylformamide and a solution of 5.4 g of sodium methoxide in 20 ml of methanol is added dropwise to the solution at 120° C. The mixture is stirred at the same temperature for 10 minutes. The reaction mixture is acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The resultant crystals are collected, washed and dried to give 8.65 g of 2-(4-nitrophenyl)benzofuran-7-carboxylic acid as pale orange powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. customevaporated
  5. customto remove solvent
  6. customThe resultant crystals are collected
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-311ff26f9dfc4930a329f93cf2b18c57
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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